Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes
Yi-Rong Chen1, Jia-Hui Han1, Weidong Rao2
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Abstract:
Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series of trifluoromethyl sulfonates were synthesized via the visible-light-induced radical addition reaction of sodium sulfinates and α-trifluoromethyl alkenes to obtain protons from the solvent. A series of dithiosulfonated derivatives were synthesized via visible-light-induced bifunctionalization reaction of α-trifluoromethyl alkenes with dithiosulfonates.This strategy has the advantages of mild reaction conditions, good substrate universality and high yield up to 99% yield.
Related Concept Videos
Preparation and Reactions of Sulfides
Introduction to Electrophilic Addition Reactions of Alkenes
Addition and elimination...
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Preparation and Reactions of Thiols
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Electrophilic Addition to Alkynes: Hydrohalogenation


